Process for the production of alpha-6-deoxytetracyclines and hydrogenation catalyst useful therein

Abstract

A coordination compound useful as a hydrogenation catalyst, having the formula: ##STR1## wherein Ph is phenyl; R is hydrogen or C 1 -C 4 alkyl; and X is chloro, bromo or iodo. This compound is particularly useful as a homogeneous hydrogenation catalyst in the production of alpha-6-deoxytetracyclines, particularly the antibiotic doxycycline. The desired alpha-6-deoxy product is produced in high yields and stereospecificities, the process requiring the use of minimal quantities of rhodium metal in the hydrogenation catalyst per mole of the 6-methylenetetracycline hydrogenated.

We claim: 
     
       1. A coordination compound useful as a hydrogenation catalyst, and having the formula: ##STR5## wherein Ph is phenyl; R is hydrogen or C 1  -C 4  alkyl; and   X is chloro, bromo or iodo.   
     
     
       2. The compound of claim 1 wherein R is hydrogen, viz., bis(triphenylphosphine) (hydroxylamine hydrochloride) dichloro rhodium (II). 
     
     
       3. The compound of claim 1, wherein R is methyl, viz., bis(triphenylphosphine) (methoxylamine hydrochloride) dichloro rhodium (II). 
     
     
       4. The compound of claim 1, wherein R is ethyl, viz., bis(triphenylphosphine) (ethoxylamine hydrochloride) dichloro rhodium (II). 
     
     
       5. The compound of claim 1, wherein R is isopropyl, viz., bis(triphenylphosphine) (isopropoxylamine hydrochloride) dichloro rhodium (II). 
     
     
       6. The compound of claim 1, wherein R is n-propyl, viz., bis(triphenylphosphine) (n-propoxylamine hydrochloride) dichloro rhodium (II).